A deoxyuridine-based far-red emitting viscosity sensor

Mengyuan Wang, Yuanwei Zhang, Xiling Yue, Sheng Yao, Mykhailo V. Bondar, Kevin D. Belfield

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

A novel deoxyuridine (dU) benzothiazolium (BZ) derivative, referred to as dU-BZ, is reported that was synthesized via Sonogashira coupling reaction methodology. The deoxyuridine building block was introduced to enhance hydrophilicity, while an alkynylated benzothiazolium dye was incorporated for long wavelength absorption to reduce potential phototoxicity that is characteristic of using UV light to excite common fluorphores, better discriminate from native autofluorescence, and potentially facilitate deep tissue imaging. An impressive 30-fold enhancement of fluorescence intensity of dU-BZ was achieved upon increasing viscosity. Fluorescence quantum yields in 99% glycerol/1% methanol (v/v) solution as a function of temperature (293-343 K), together with viscosity-dependent fluorescence lifetimes and radiative and non-radiative rate constants in glycerol/methanol solutions (ranging from 4.8 to 950 cP) were determined. Both fluorescence quantum yields and lifetimes increased with increased viscosity, consistent with results predicted by theory. This suggests that the newly-designed compound, dU-BZ, is capable of functioning as a probe of local microviscosity, an aspect examined by in vitro bioimaging experiments.

Original languageEnglish (US)
Article number709
JournalMolecules
Volume21
Issue number6
DOIs
StatePublished - Jun 1 2016

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Keywords

  • Bioimaging
  • Far-red fluorescent probe
  • Microviscosity sensor
  • Molecular rotor
  • Nucleosides
  • Sonogashira coupling

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